When Passion Turns to a Job: The Challenges of Going Self-Employed

“Find a job you love doing and you’ll never have to work another day.”

Hmm. Not necessarily. Trust me, you will need to work. 

In a few days it will have been one year since I started working freelance. It has been great, but it has also been one bumpy ride. Shifting from full employment to self-employment started out as an exciting adventure and has turned into a huge challenge that I am now willingly taking on.

I was offered to be a remote contractor as the Managing Editor of www.mscareergirl.com, a website that helps women achieve success in their career and personal lives. It touched on three things that I absolutely loved –  writing, empowering women, and working from home. It was perfect. It was a job that I love, and as the quote implies, this should mean that I shouldn’t ever feel like I’m working or stress out at all. Ever. 


This quote, however, was a lie. Since I’ve left the corporate world, all I have been doing is WORK. 


The Challenge of Setting Yourself Up

The first struggle was working on the technical side of things. Since I was going freelance, I decided to set up my business, Upraise Marketing Services. For the first time in my professional life, I had no HR team to set up my company documents and government requirements. I had no finance department to arrange and deposit my payroll to my bank. I had no IT guy to set up my computer or the systems within it. I had no one. I did not even have a desk. 

When you jump ship from the corporate world, you can feel quite alone and lost. I luckily had a client who was used to working with remote contractors, so he was able to give me a lot of advice on how to set up shop, but it took a lot of researching, trial and error, and self motivation before I finally felt like I have finally settled into my new self-employed status. I also bought myself a desk. (Actually using it regularly is a struggle, but I’m working on it!) 

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Creative Challenges

The next problem was the creative side of things. Turning your passion into your form of income is a tricky thing. If you are a singer and you sang the same song in front of an audience every night, five times a week, there will be a time that you wouldn’t even want to let out a single note. Writing, as a job, is the same thing. I have done it so much that there was a time that I just started hating it. I constantly had writer’s block, to the point that I couldn’t get a single sentence out of me to answer the question “what do I wear to my first interview?”. It also made me question if I’m even qualified to help other women, when I am obviously in limbo with my career as well. It was tough, as it always seems to end up with the question “WTF are you doing?!”

When times like this happened, all I had to hold on to was the reminder that I’m actually doing something I love doing. I realized that by giving myself some space, I am able to work better. I learned to take care of myself, take a break, communicate better with other people,  and make avenues for me to still express myself. This is how the Upraised Living blog came to be. 


Challenging Old Attitudes on being Self-Employed

I’m not saying that I have it all figured out though. Hell, I don’t think I’m that quite settled, actually. Being self-employed has turned me restless. I became my own boss. The thing with working for yourself is that you feel much more pressure to push yourself and find another level to your work. You are always in constant fear that you might lose your client, and in the mindset that you need to get more means of generating income. You expect more from yourself. You try to learn as much as you can and you try to work as wisely as you can. You have to make decisions, goals, and efforts on your own. YOU are your product. You have to develop and sell yourself. 


So no, you don’t get to sit back and put your feet up. Being my own boss meant more work physically, creatively, and emotionally, but it also meant greater rewards. I think many freelancers don’t bother setting themselves up or even considering themselves as a business for different reasons. Some are too busy, some don’t know where to begin, some just don’t really care much. Trust me when I say this – setting my business up was a rewarding experience. Putting systems in place, registering myself with official documents, creating goals for my own self as a business and working towards accomplishing them is an accomplishment that no one can take away from you. Like I said, I am still in the process of growing and learning, and it’s both a challenge and an advantage to the new life that I took on.  


I learned that when a passion turns into your job, you need to put more work into sustaining and growing that passion. Finding a job you love doesn’t stop the work. It makes you want to – willingly and happily – work more. 





5 thoughts on “When Passion Turns to a Job: The Challenges of Going Self-Employed

    • Thank you for the comment. I feel that it is nice that we can now learn from other people’s experiences. I’m glad to share mine with you! Will definitely keep myself posted on your journey through your blog!

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